Cyclopentene, 3-methyl-

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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas9.67kJ/molChydAllinger, Dodziuk, et al., 1982 
Δfgas7.36 ± 0.71kJ/molCmFuchs and Peacock, 1979 
Δfgas8. ± 2.kJ/molCcbLabbauf and Rossini, 1961Heat of formation derived by Cox and Pilcher, 1970

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Cyclopentene, 3-methyl- + Hydrogen = Cyclopentane, methyl-

By formula: C6H10 + H2 = C6H12

Quantity Value Units Method Reference Comment
Δr-115.4 ± 0.75kJ/molChydAllinger, Dodziuk, et al., 1982liquid phase; solvent: Hexane

Cyclopentene, 1-methyl- = Cyclopentene, 3-methyl-

By formula: C6H10 = C6H10

Quantity Value Units Method Reference Comment
Δr8.1 ± 0.3kJ/molEqkYursha and Kabo, 1975gas phase

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H10+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.95EILossing and Traeger, 1975LLK
8.95 ± 0.01PERang, Paldoia, et al., 1974LLK
8.99 ± 0.04EIWinters and Collins, 1969RDSH
8.98 ± 0.05PEMcAlduff, Caramella, et al., 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.24 ± 0.32?EIWinters and Collins, 1969RDSH
C3H5+12.28 ± 0.17?EIWinters and Collins, 1969RDSH
C4H5+12.69 ± 0.20?EIWinters and Collins, 1969RDSH
C4H6+10.69 ± 0.07?EIWinters and Collins, 1969RDSH
C5H5+13.35 ± 0.05?EIWinters and Collins, 1969RDSH
C5H7+8.95CH3EILossing and Traeger, 1975, 2LLK
C5H7+10.03CH3EILossing and Traeger, 1975LLK
C5H7+9.67 ± 0.11CH3EIWinters and Collins, 1969RDSH
C5H7+10.52CH3EIPignataro, Cassuto, et al., 1967RDSH
C6H7+11.75 ± 0.04H2+HEIWinters and Collins, 1969RDSH
C6H9+10.35 ± 0.17HEIWinters and Collins, 1969RDSH

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryDB-140.610.Lubeck and Sutton, 198460. m/0.264 mm/0.25 μm, H2
CapillaryHP-PONA40.610.Lubeck and Sutton, 198450. m/0.21 mm/0.5 μm, H2
CapillarySE-3080.615.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
CapillarySqualane50.605.5Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.606.5Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane100.611.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane27.600.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane30.600.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane50.603.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane67.608.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane70.607.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane80.607.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane86.610.Bogoslovsky, Anvaer, et al., 1978 
CapillarySqualane100.610.Rang, Orav, et al., 1977Nitrogen or helium; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane100.604.Lulova, Leont'eva, et al., 1976He; Column length: 120. m; Column diameter: 0.25 mm
CapillarySqualane100.611.Dielmann, Schwengers, et al., 1974Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane80.607.Dielmann, Schwengers, et al., 1974Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane50.603.Rijks and Cramers, 1974N2; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.606.Rijks and Cramers, 1974N2; Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane27.600.00Schomburg and Dielmann, 1973Column length: 100. m; Column diameter: 0.25 mm
CapillaryApiezon L100.627.Eisen, Orav, et al., 1972Column length: 45. m; Column diameter: 0.25 mm
CapillaryApiezon L120.633.Eisen, Orav, et al., 1972Column length: 45. m; Column diameter: 0.25 mm
CapillarySqualane30.601.5Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane60.605.8Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane80.607.7Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane30.602.Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane60.606.Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
CapillarySqualane80.608.Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
PackedSE-3075.615.Robinson and Odell, 1971N2, Chromosorb W; Column length: 6.1 m
PackedSqualane100.609.Robinson and Odell, 1971N2, Embacel; Column length: 3.0 m
PackedSqualane27.601.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.604.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.608.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.610.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
CapillarySqualane50.607.Schomburg, 1966 

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH-100611.4Haagen-Smit Laboratory, 1997He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min)

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG 4000100.736.Rang, Orav, et al., 1988 
CapillaryPEG 400060.726.Rang, Orav, et al., 1988 
CapillaryPEG 400080.729.Rang, Orav, et al., 1988 
CapillaryPEG 4000100.736.Rang, Orav, et al., 1977Nitrogen or Helium; Column length: 45. m; Column diameter: 0.25 mm
CapillaryPolyethylene Glycol 4000100.735.8Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPolyethylene Glycol 400060.725.6Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPolyethylene Glycol 400080.728.7Eisen, Orav, et al., 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPEG 4000100.735.8Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPEG 400060.725.6Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm
CapillaryPEG 400080.728.7Orav and Eisen, 1972Column length: 80. m; Column diameter: 0.25 mm

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone637.44Hassoun, Pilling, et al., 199950. m/0.25 mm/1. μm, He; Program: -50C(2min) => 49.9C/min => 35C(10min) => 3C/min => 200C(2min) => 40C/min => 240C(30min)

Normal alkane RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySE-5450.620.Xieyun, Maoqi, et al., 1996N2; Column length: 40. m; Column diameter: 0.25 mm

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane: CP-Sil 5 CB610.Bramston-Cook, 201360. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
CapillaryPetrocol DH588.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
CapillaryPetrocol DH606.Supelco, 2012100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min
CapillaryPONA609.Zhang, Ding, et al., 200950. m/0.20 mm/0.50 μm, Nitrogen, 35. C @ 15. min, 2. K/min, 200. C @ 10. min
CapillarySE-54607.Guan, Li, et al., 199560. C @ 2. min, 4. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tend: 200. C
CapillaryDB-1608.Ramnas, Ostermark, et al., 199450. m/0.32 mm/1.0 μm, He, 2. K/min; Tstart: -20. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySqualane615.Chen, 2008Program: not specified
CapillarySqualane607.Chen, 2008Program: not specified
CapillaryPONA612.Perkin Elmer Instruments, 2002Column length: 100. m; Phase thickness: 0.50 μm; Program: not specified
CapillaryDB-5 MS656.Luo and Agnew, 200130. m/0.25 mm/1.0 μm, Helium; Program: not specified
CapillaryMethyl Silicone611.Spieksma, 1999Program: not specified
PackedSE-30619.Robinson and Odell, 1971N2, Chromosorb W; Column length: 6.1 m; Program: 50C910min) => 20C/min => 90(6min) => 10C/min => 150C(hold)
PackedSqualane598.Robinson and Odell, 1971N2, Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min => 35 => 4C/min => 95C(hold)
PackedSE-30619.Robinson and Odell, 1971, 2Chrom W; Column length: 6.1 m; Program: 50C(10min) => 20C/min(2min) => 90C(6min) => 10C/min(6min) => (hold at 150C)
PackedSqualane598.Robinson and Odell, 1971, 2Embacel; Column length: 3.0 m; Program: 25C(5min) => 2C/min(5min) => 4C/min(15min) => (hold at 95C)

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Allinger, Dodziuk, et al., 1982
Allinger, N.L.; Dodziuk, H.; Rogers, D.W.; Naik, S.N., Heats of hydrogenation and formation of some 5-membered ring compounds by molecular mechanics calculations and direct measurements, Tetrahedron, 1982, 38, 1593-1597. [all data]

Fuchs and Peacock, 1979
Fuchs, R.; Peacock, L.A., Heats of vaporization and gaseous heats of formation of some five- and six-membered ring alkenes, Can. J. Chem., 1979, 57, 2302-2304. [all data]

Labbauf and Rossini, 1961
Labbauf, A.; Rossini, F.D., Heats of combustion, formation, and hydrogenation of 14 selected cyclomonoolefin hydrocarbons, J. Phys. Chem., 1961, 65, 476-480. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Yursha and Kabo, 1975
Yursha, I.A.; Kabo, G.Ya., Thermodynamics of the isomerisation of methylcyclopentines, Russ. J. Phys. Chem. (Engl. Transl.), 1975, 49, 765-766. [all data]

Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C., Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations, J. Am. Chem. Soc., 1975, 97, 1579. [all data]

Rang, Paldoia, et al., 1974
Rang, S.; Paldoia, P.; Talvari, A., Ionization potentials of unsaturated hydrocarbons. 2. Mono-substituted cyclopentenes and cyclohexenes, Eesti. NSV Tead. Akad. Toim., 1974, 354. [all data]

Winters and Collins, 1969
Winters, R.E.; Collins, J.H., Mass spectrometric studies of structural isomers. II.Mono- and bicyclic C6H10 molecules, Org. Mass Spectrom., 1969, 2, 299. [all data]

McAlduff, Caramella, et al., 1978
McAlduff, E.J.; Caramella, P.; Houk, K.N., Photoelectron spectra of 3-substituted cyclopentenes. Correlations between ionization potentials and cycloaddition regioselectivity, J. Am. Chem. Soc., 1978, 100, 105. [all data]

Lossing and Traeger, 1975, 2
Lossing, F.P.; Traeger, J.C., Free radicals by mass spectrometry XLVI. Heats of formation of C5H7 and C5H9 radicals and cations., J. Am. Chem. Soc., 1975, 19, 9. [all data]

Pignataro, Cassuto, et al., 1967
Pignataro, S.; Cassuto, A.; Lossing, F.P., Free radicals by mass spectrometry. XXXVI. Ionization potentials of conjugated and nonconjugated radicals, J. Am. Chem. Soc., 1967, 89, 3693. [all data]

Lubeck and Sutton, 1984
Lubeck, A.J.; Sutton, D.L., Kovats Retention Indices of Selected Olefins on Bonded Phase Fused Silica Capillaries, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1984, 7, 9, 542-544, https://doi.org/10.1002/jhrc.1240070913 . [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Bajus, Veselý, et al., 1979
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 2. Pyrolysis of methylcyclohexane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 2, 135-142, https://doi.org/10.1021/i360070a012 . [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Rang, Orav, et al., 1977
Rang, S.; Orav, A.; Kuningas, K.; Eisen, O., Capillary Gas Chromatography of Monosubstituted Cyclopentenes and Cyclohexenes, Chromatographia, 1977, 10, 3, 115-122, https://doi.org/10.1007/BF02297862 . [all data]

Lulova, Leont'eva, et al., 1976
Lulova, N.I.; Leont'eva, S.A.; Timofeeva, A.N., Gas-chromatographic method of determination of individual hydrocarbons in catalytic cracking gasolines in Proceedings of All-Union Research Institute on Oil Processes. Vol.18, All-Union Research Institute on Oil Processes, Moscow, 1976, 30-53. [all data]

Dielmann, Schwengers, et al., 1974
Dielmann, G.; Schwengers, D.; Schomburg, G., Gas-chromatographische Retentionsdaten und Strukture chemischer Verbindungen Gesättigte und ungesättigte alkylsubstituierte Cyclopentane und Methylcyclopentane, Chromatographia, 1974, 7, 5, 215-224, https://doi.org/10.1007/BF02321771 . [all data]

Rijks and Cramers, 1974
Rijks, J.A.; Cramers, C.A., High precision capillary gas chromatography of hydrocarbons, Chromatographia, 1974, 7, 3, 99-106, https://doi.org/10.1007/BF02269819 . [all data]

Schomburg and Dielmann, 1973
Schomburg, G.; Dielmann, G., Identification by means of retention parameters, J. Chromatogr. Sci., 1973, 11, 3, 151-159, https://doi.org/10.1093/chromsci/11.3.151 . [all data]

Eisen, Orav, et al., 1972
Eisen, O.; Orav, A.; Rang, S., Identifizierung von Normal-Alkenen, Cyclopentenen und -Hexenen mittels Kapillar-Gas-Chromatographie. Identification des alcènes, cyclopentènes et -hexènes à l'aide de la chromatogrpahie en phase gazeuse sur colonne capillaire, Chromatographia, 1972, 5, 11, 229-239, https://doi.org/10.1007/BF02270600 . [all data]

Orav and Eisen, 1972
Orav, A.; Eisen, O., The retention indexes for alkenes, alkynes and cyclenes on capillary columns, Izv. Akad. Nauk Est. SSR, Khim. Geol., 1972, 21, 1, 39-47. [all data]

Robinson and Odell, 1971
Robinson, P.G.; Odell, A.L., A system of standard retention indices and its uses. The characterisation of stationary phases and the prediction of retention indices, J. Chromatogr., 1971, 57, 1-10, https://doi.org/10.1016/0021-9673(71)80001-8 . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe, J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4 . [all data]

Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory, Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]

Rang, Orav, et al., 1988
Rang, S.A.; Orav, A.E.; Kuningas, K.R.; Meister, A.E.; Strense, T.V.; Eisen, O.G., Gas-Chromatographic Characteristics of unsaturated hydrocarbons, Academy of Sciences of Estonia SSR, Tallinn, Estonia SSR, 1988, 208. [all data]

Hassoun, Pilling, et al., 1999
Hassoun, S.; Pilling, M.J.; Bartle, K.D., A catalogue of urban hydrocarbons for the city of Leeds: atmospheric monitoring of volatile organic compounds by thermal desorption-gas chromatography, J. Environ. Monitor., 1999, 1, 5, 453-458, https://doi.org/10.1039/a904879k . [all data]

Xieyun, Maoqi, et al., 1996
Xieyun, H.; Maoqi, C.; Shiyan, Y., Gas Chromatographic analysis during the process of heptaldehyde production using 1-hexene, Chin. J. Chromatogr., 1996, 14, 4, 291-293. [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]

Supelco, 2012
Supelco, CatalogNo. 24160-U, Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]

Zhang, Ding, et al., 2009
Zhang, X.; Ding, L.; Sun, Z.; Song, L.; Sun, T., Study on quantitative structure-retention relationships for hydrocarbons in FCC gasoline, Chromatographia, 2009, 70, 3/4, 511-518, https://doi.org/10.1365/s10337-009-1174-0 . [all data]

Guan, Li, et al., 1995
Guan, Y.; Li, L.; Zhou, L., Live retention database for compound identification in capillary gas chromatography, Chin. J. Chromatogr., 1995, 13, 5, 851-857. [all data]

Ramnas, Ostermark, et al., 1994
Ramnas, O.; Ostermark, U.; Peterson, G., Characterization of sixty alkenes in a cat-cracked gasoline naphtha by gas chromatography, Chromatographia, 1994, 38, 3/4, 222-226, https://doi.org/10.1007/BF02290340 . [all data]

Chen, 2008
Chen, H.-F., Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression, Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003 . [all data]

Perkin Elmer Instruments, 2002
Perkin Elmer Instruments, Detailed hydrocarbon analysis (DHAX) Model 4015, 2002, retrieved from http://www.perkinelmer.com/instruments. [all data]

Luo and Agnew, 2001
Luo, J.; Agnew, M.P., Gas characteristics before and after biofiltration treating odorous emissions from animal rendering processes, Environ. Technol., 2001, 22, 9, 1091-1103, https://doi.org/10.1080/09593332208618220 . [all data]

Spieksma, 1999
Spieksma, W., Determination of vapor liquid equilibrium from the Kovats retention index on dimethylsilicone using the Wilson mixing tool, J. Hi. Res. Chromatogr., 1999, 22, 10, 565-588, https://doi.org/10.1002/(SICI)1521-4168(19991001)22:10<565::AID-JHRC565>3.0.CO;2-2 . [all data]

Robinson and Odell, 1971, 2
Robinson, P.G.; Odell, A.L., Comparison of isothermal and non-linear temperature programmed gas chromatography. The temperature dependence of the retention indices of a number of hydrocarbons on squalane and SE-30, J. Chromatogr., 1971, 57, 11-17, https://doi.org/10.1016/0021-9673(71)80002-X . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References